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Volume 68 
Part 1 
Page o166  
January 2012  

Received 26 November 2011
Accepted 13 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.110
Data-to-parameter ratio = 19.2
Details
Open access

(E)-4-Chloro-N-[4-(methylsulfonyl)benzylidene]aniline

aSchool of Life Sciences, ShanDong University of Technology, ZiBo 255049, People's Republic of China
Correspondence e-mail: njuqss@yahoo.com.cn

In the crystal structure of the title compound, C14H12ClNO2S, the molecules display a trans conformation with respect to the C=N double bond. The dihedral angle between the methylsulfonyl benzene and chlorobenzene rings is 59.59 (8)°. The crystal packing is stabilized by weak C-H...O interactions and by [pi]-[pi] stacking interactions between inversion-related methylsulfonyl benzene rings [centroid-centroid distance = 3.8579 (11) Å].

Related literature

For background to the pharmacological properties of Schiff base compounds, see: Villar et al. (2004[Villar, R., Encio, I., Migliaccio, M., Gil, M. J. & Martinez-Merino, V. (2004). Bioorg. Med. Chem. 12, 963-968.]); Pandey et al. (1999[Pandey, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624-628.]); Singh & Dash (1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]). For related structures, see: Qian & Cui (2009[Qian, S.-S. & Cui, H.-Y. (2009). Acta Cryst. E65, o3093.]); Qian & Liu (2010[Qian, S.-S. & Liu, T. (2010). Acta Cryst. E66, o18.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO2S

  • Mr = 293.77

  • Monoclinic, P 21 /n

  • a = 8.6206 (10) Å

  • b = 8.8748 (10) Å

  • c = 17.799 (2) Å

  • [beta] = 94.972 (1)°

  • V = 1356.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 296 K

  • 0.25 × 0.23 × 0.21 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.898, Tmax = 0.913

  • 11492 measured reflections

  • 3320 independent reflections

  • 2596 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.110

  • S = 1.04

  • 3320 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O1i 0.93 2.56 3.126 (2) 120
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2372 ).


Acknowledgements

This project was sponsored by the ShanDong Province Science & Technology Innovation Foundation (People's Republic of China).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Pandey, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624-628.  [PubMed]
Qian, S.-S. & Cui, H.-Y. (2009). Acta Cryst. E65, o3093.  [CSD] [CrossRef] [details]
Qian, S.-S. & Liu, T. (2010). Acta Cryst. E66, o18.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.
Villar, R., Encio, I., Migliaccio, M., Gil, M. J. & Martinez-Merino, V. (2004). Bioorg. Med. Chem. 12, 963-968.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o166  [ doi:10.1107/S160053681105361X ]

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